GB2107693A - Organophilic organic-clay complexes - Google Patents
Organophilic organic-clay complexes Download PDFInfo
- Publication number
- GB2107693A GB2107693A GB08134467A GB8134467A GB2107693A GB 2107693 A GB2107693 A GB 2107693A GB 08134467 A GB08134467 A GB 08134467A GB 8134467 A GB8134467 A GB 8134467A GB 2107693 A GB2107693 A GB 2107693A
- Authority
- GB
- United Kingdom
- Prior art keywords
- clay
- organic
- group
- cation
- smectite
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004927 clay Substances 0.000 title claims description 89
- -1 organic cation salt compound Chemical class 0.000 claims description 68
- 150000002891 organic anions Chemical class 0.000 claims description 49
- 150000002892 organic cations Chemical class 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000003349 gelling agent Substances 0.000 claims description 16
- 238000005341 cation exchange Methods 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002015 acyclic group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 claims description 5
- 229910000271 hectorite Inorganic materials 0.000 claims description 5
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000004714 phosphonium salts Chemical class 0.000 claims description 2
- ONCZQWJXONKSMM-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4].[Si+4].[Si+4].[Si+4] ONCZQWJXONKSMM-UHFFFAOYSA-N 0.000 claims 2
- 229940080314 sodium bentonite Drugs 0.000 claims 2
- 229910000280 sodium bentonite Inorganic materials 0.000 claims 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 125000005313 fatty acid group Chemical group 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000011734 sodium Substances 0.000 description 64
- 230000008961 swelling Effects 0.000 description 25
- 239000003760 tallow Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 20
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 7
- 150000001768 cations Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000012530 fluid Substances 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 235000012216 bentonite Nutrition 0.000 description 5
- 150000001767 cationic compounds Chemical class 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 229940070765 laurate Drugs 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- 125000005474 octanoate group Chemical group 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 239000000440 bentonite Substances 0.000 description 4
- 229910000278 bentonite Inorganic materials 0.000 description 4
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 4
- 229960001860 salicylate Drugs 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- CBJQOQIFFROSDQ-UHFFFAOYSA-N C(C(C)C)C(=O)C.C(CCCCCCC(C)C)C(C1=CC=CC=C1)CCCCCCCC(C)C Chemical compound C(C(C)C)C(=O)C.C(CCCCCCC(C)C)C(C1=CC=CC=C1)CCCCCCCC(C)C CBJQOQIFFROSDQ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 3
- HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- OKXAFOJPRGDZPB-UHFFFAOYSA-N dioctadecoxy(oxo)phosphanium Chemical compound CCCCCCCCCCCCCCCCCCO[P+](=O)OCCCCCCCCCCCCCCCCCC OKXAFOJPRGDZPB-UHFFFAOYSA-N 0.000 description 3
- HQWKKEIVHQXCPI-UHFFFAOYSA-L disodium;phthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C([O-])=O HQWKKEIVHQXCPI-UHFFFAOYSA-L 0.000 description 3
- 229910052621 halloysite Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KIHBGTRZFAVZRV-UHFFFAOYSA-M 2-hydroxyoctadecanoate Chemical compound CCCCCCCCCCCCCCCCC(O)C([O-])=O KIHBGTRZFAVZRV-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical group 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- KWHDXJHBFYQOTK-UHFFFAOYSA-N heptane;toluene Chemical compound CCCCCCC.CC1=CC=CC=C1 KWHDXJHBFYQOTK-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000009830 intercalation Methods 0.000 description 2
- 230000002687 intercalation Effects 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/155—Colour-developing components, e.g. acidic compounds; Additives or binders therefor; Layers containing such colour-developing components, additives or binders
- B41M5/1555—Inorganic mineral developers, e.g. clays
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M113/00—Lubricating compositions characterised by the thickening agent being an inorganic material
- C10M113/16—Inorganic material treated with organic compounds, e.g. coated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/346—Clay
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/104—Aromatic fractions
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/106—Naphthenic fractions
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/063—Ammonium or amine salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S507/00—Earth boring, well treating, and oil field chemistry
- Y10S507/901—Organically modified inorganic solid
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S507/00—Earth boring, well treating, and oil field chemistry
- Y10S507/926—Packer fluid
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Wood Science & Technology (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
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Description
1
SPECIFICATION
Anionically modified organophilic clays GB 2 107 693 A 1 This invention relates to organophilic organic-clay complexes which are dispersible in organic liquids to form a gel therein. Depending on the composition of the gel, such gels may be useful as lubricating greases, oil base muds, oil base packerfluids, paint-varnish-lacquer removers, paints, foundry molding sand binders, adhesives and sealants, inks, polyester laminating resins, polyester gel coats, and the like.
It is well known that organic compounds which contain a cation will react under favorable conditions by ion-exchange with clays which contain a negative layer-lattice and exchangeable cations to form organophilic organic-clay products. If the organic cation contains at least one alkyl group containing at least 10 carbon atoms, then such organoclays have the property of swelling in certain organic liquids. See for Example U.S. Pat. No. 2,531,427 and U.S. Pat. No. 2,966,506, both incorporated herein by reference, and the book "Clay Mineralogy", 2nd Edition, 1968 by Ralph E. Grim (McGraw-Hill Book Company, Inc.), particularly Chapter 10, Clay-Mineral-Organic Reactions; pp. 356-368 - Ionic Reactions, Smectite; and pp. 392-401 - 15 Organophilic Clay-Mineral Complexes.
It is also known that organic compounds presented in the anionic form are usually repelled by, rather than attracted to, the negatively charged clay surface. This effect is referred to as negative adsorption. However, positive adsorption of anions can occur under conditions in which such compounds exist in the molecular, i.e., undissociated form. See "Chemistry of Clay -Organic Reactions" 1974 by B.K.G. Theng, John Wiley& 20 Sons.
In contrast, Wada found that this phenomena, i.e., adsorption, does occur with certain ionic compounds when reacted with halloysite, kanolinite group material, to form intersalates. Intersalation was achieved by grinding the mineral with moist crystals of salts of low molecular weight carboxylic acids or by contacting the mineral with saturated solutions. This interlayer complex contained the complete salt as well as water. 25 The intersalated material however was removed by washing with water resulting in either hydration of the interlayer or collapse to the original spacing. No evidence of variation in basal spacing was found with montmorillonite treated with salts in contrast with halloysite. See TheAmerican Minerologist, Volume 44, 1959, by K. Wada "Oriented Penetrationof Ionic Compounds between the Silicate Layers of Halloysite".
Since the commercial introduction of organoclays in the early 1950's, it has become well known that maximum gelling (thickening) efficiency from these organoclays is achieved by adding a low molecular weight polar organic material to the composition. Such polar organic materials have been variously called dispersants, dispersion aids, solvating agents, dispersion agents and the like. See for example the following U.S. Patents: O'Halloran 2,677,661; McCarthy et al. 2,704,276; Stratton 2, 833,720; Stratton 2,879,229; Stansfield et al. 3,294,683. The use of such dispersion aids was found unnecessary when using specially 35 designed organophilic clays derived from substituted quaternary ammonium compounds. See U.S. Patents:
Finlayson et al. 4,105,578 and Finlayson 4,208,218.
In contrast to the prior art organoclay compositions, a self-activating rheological agent has been unexpectedly produced which does not require the addition of polar solvent activators, which agent is produced from the reaction of an organic cation, an organic anion and a smectite-type clay.
An organophilic clay gellant having enhanced dispersibility in nonaqueous systems has been unexpectedly discovered which comprises the reaction product of:
a. an organic cation salt compound, wherein said organic cation has the formula:
-1 + 45 R, 1 R4.- X- R2 50 1 1.1? 5 L wherein R, is selected from the group consisting of a 13, V-unsaturated alkyl group and a hydroxyalkyl group having 2 to 6 carbon atoms and mixtures thereof; R2 is a long chain alkyl group having 12 to 60 carbon atoms; R3 and R4 are individually selected from the group consisting of a P, y-unsaturated alkyl group, a hydroxyalkyl group having 2 to 6 carbon atoms, an aralkyl group, an alkyl group having from 1 to 22 carbon 60 atoms and mixtures thereof; Xis selected from a group consisting of phosphorous and nitrogen; b. an organic anion; and c. a smectite-type clay having a cation exchange capacity of at least 75 milliequivalents per 100 grams of said clay; such that an organic cation - organic anion complex is intercalated with the smectite-type clay and the cation 65 exchange sites of the smectite-type clay are substituted with the organic cation.
2 GB 2 107 693 A 2 The organophilic clays of the invention may be prepared by admixing the organic anion with a clay and water together, preferably at a temperature between 200C and 1 OOOC, preferably between 350 and 77'C for a sufficient time to prepare a homogeneous mixture followed by the addition of the organic cation in sufficient amounts to satisfy the cation exchange capacity of the clay and the cationic capacity of the organic anion.
The order of addition of the organic cation and organic anion is not significant as long as a sufficient amount of organic cation is added. In fact, the appropriate quantities of organic cation and sodium salt of the organic anion, in solution (water and/or 2-propanol) at a 20 to 90% solids basis, may be premixed to form an organic cation-organic anion complex and then added as a solution to react with the clay slurry. After addition of the organic anion and organic cation, the mixture is reacted with agitation at a temperature between 200C and 1 00'C preferably between 35' and 77'C fora sufficient time to allow the formation of an organic cation-organic anion complex which is intercalated with the clay and the cation exchange sites of the clay are substituted with the organic cation. Reaction temperatures below 20'C or above 100'C while useable are not preferred.
The addition of the organic cation and organic anion may be done either separately or as a complex. In using the organophilic clays in emulsions, the drying and grinding steps may be eliminated. When the clay, 15 organic cation, organic anion and water are mixed in such concentrations then a slurry is notformed, the filtration and washing steps can be eliminated.
The clay is preferably dispersed in water at a concentration from about 1 to 80% and preferably 2% to 7% to form a clay slurry. The clay slurry may be optionally centrifuged to remove non-clay impurities which constitute about 10% to about 50% of the starting clay composition. The slurry is generally pre-heated under 20 agitation to a temperature in the range from 35'C to 77oC before the addition of the organic reactants.
The amount of organic anion added to the clay for purposes of this invention should be sufficient to impart to the organophilic clay the enhanced dispersion characteristic desired. This amount is defined as the millequivalent ratio which is the number of milliequivalents (M.E.) of the organic anion in the organoclay per 100 grams of clay, 100% active clay basis. The organophilic clays of this invention should preferably have an 25 anion milliequivalent ratio of 5 to 100 and more preferably 10 to 50.
The organic anion is preferably added to the reactants in the desired milliequivalent ratio as a solid or solution in water under agitation to effect a homogenous mixture.
The organic cation should be employed in a sufficient quantity to at least satisfy the cation exchange capacity of the clay and the cationic activity of the organic anion. Additional cation above the sum of the 30 exchange capacity of the clay and anion may be optionally used. It has been found that use of at least 90 milliequivalents of organic cation is sufficient to satisfy a portion of the total organic cation requirement. Use of amounts from 80 to 200 M.E. - and preferably from 100 to 160 M.E. are acceptable.
For convenience of handling it is preferred that the total organic content of the organophilic clay reaction products of this invention should be less than about 50% by weight of the organoclay. Higher amounts are 35 usable, but the reaction product is difficult to process.
Another process for preparing the organophilic clays of this invention comprises:
a. slurrying a smectite-type clay in water at 1 to 80% by weight of said clay; b. heating the slurry to a temperature between 20'C and 100'C; c. adding 5 to 100 milliequivalents of an organic anion per 100 grams of clay, 100% active clay basis and 40 the organic cation in a sufficient amount to satisfy the cation exchange capacity of the smectite-type clay and the cationic activity of the organic anion while agitating the reaction solution; d. reacting the mixture fora sufficient time to form a reaction product comprising an organic cation-organic anion complex which is intercalated with the smectite-type clay and the cation exchange sites of the smectite-type clay are substituted with the organic cation; and e. recovering the reaction product.
The organic cationic compound useful in this invention may be selected from a wide range of materials that are capable of forming an organophilic clay by exchange of cations with the smectite-type clay. The organic cationic compound must have a positive charge localized on a single atom or on a small group of atoms within the compound. Preferably the organic cation is selected from the group consisting of quarternary ammonium salts, phosphonium salts, and mixtures thereof, as well as equivalent salts. The organic cation preferably contains at least one member selected from each of two groups, the first group consisting of (a) a P, y-unsaturated alkyl group, and (b) a hydroxyalkyl group having 2 to 6 carbon atoms, and the second consisting of a long chain alkyl group. The remaining moieties on the central positive atom are chosen from a member from a 0, y-unsaturated alkyl group and/or a hydroxyalkyl group having 2 to 6 carbon 55 atoms or an aralkyl group and/or an alkyl group having from 1 to 22 carbon atoms.
1 4 3 A representative formula of the cationic compound is:
1 F_ R, 1 1 R4- X - R? 1 RS GB 2 107 693 A 3 wherein R, is selected from the group consisting of a P, y-u nsatu rated alkyl group and a hydroxyalkyl group having 2 to 6 carbon atoms; R2 is a long chain alkyl group having 12 to 60 carbon atoms; R3 and R4 are selected from a group consisting of a 0, y-unsaturated alkyl group, a hydroxyalkyl group having 2 to 6 carbon atoms, an aralkyl group, and an alkyl group having from 1 to 22 carbon atoms; Xis phosphorous or nitrogen. 15 R, The P,,y-u nsatu rated alkyl group may be selected from a wide range of materials. These compounds may be cyclic or acyclic, unsubstituted or substituted. P, y-unsaturated alkyl radicals preferably contain less than 7 aliphatic carbon atoms. P, y-unsaturated alkyl radicals substituted with an aliphatic radical preferably contains less than 4 aliphatic carbons. The P, y-unsaturated alkyl radical may be substituted with an aromatic ring that likewise is conjugated with the unsaturation of the P, y moiety or the P, y-radical is substituted with both an aliphatic radical and aromatic ring.
Representative examples of cyclic P, y-unsaturated alkyl groups include 2cyclohexenyl and 2cyclopentenyl. Representative examples of acyclic P, yunsaturated alkyl groups containing 6 or less carbon 25 atoms include propargyl; 2-propenyl; 2-butenyl; 2-pentenyl; 2-hexenyl; 3-methyl-2butenyl; 3-methyl-2pentenyl- 2,3-dimethyl-2-butenyl; 1,1-dimethyl-2propenyl; 1,2-dimethyl propenyl; 2,4-pentadienyl; and 2,4-hexadienyl; Representative examples of acyclic-aromatic substituted compounds include 3-phenyl-2propenyl; 2-phenyl-2-propenyl and 3-(-4-methoxyphenyl)-2-propenyl. Representative examples of aromatic and aliphatic substituted materials include 3-phenyl-2-cyclohexenyl; 3phenyl-2-cyclopentenyl; alkyl group may be substituted with an aromatic ring.
The hydroxyalkyl group is selected from a hydroxyl substituted aliphatic radical wherein the hydroxyl is not substituted at the carbon adjacent to the positively charged atom and the group has from 2 to 6 aliphatic carbons. The alkyl group maybe substituted with an aromatic ring. Representative examples include 2-hydroxyethyl; 3-hydroxypropyl; 4hydroxypentyl; 6-hydroxyhexyl; 2-hydroxypropyl; 2-hydroxybutyl; 2hydroxypentyl; 2-hydroxyhexyl; 2-hydroxycyclohexyl; 3-hydroxycyclohexyl; 4-hydroxycyclohexyl; 2hydroxycyclopentyl; 3-hydroxycyclopentyl; 2-methyl2-hydroxypropyl; 3-methyl-2-hydroxybutyl; and 5hydroxy-2-pentenyl.
R2 The long chain alkyl radicals may be branched or unbranched, saturated or unsaturated, substituted or unsubstituted and should have from 12 to 60 carbon atoms in the straight chain portion of the radical.
The long chain alkyl radicals may be derived from natural occurring oils including various vegetable oils, such as corn oil, coconut oil, soybean oil, cottonseed oil, castor oil and the like, as well as various animal oils 45 or fats such as tallow oil. The alkyl radicals may likewise be petrochernically derived such as from alpha olefins.
Representative examples of useful branched, saturated alkyl radicals include 12-methyl stearyl; and 12-ethyl stearyl. Representative examples of useful branched, unsaturated radicals include 12-methyloleyl and 12-ethyloleyl. Representative examples of unbranched saturated radicals include lauryl; stearyl; tridecyl; myristal (tetradecyl); pentadecyl; hexadecyl; hydrogenated tallow, and docosonyl; Representative examples of unbranched, unsaturated and unsubstituted long chain alkyl radicals include oleyl, linoleyl; linolenyl, soya and tallow.
R3andR4 The remaining groups on the positive charged atom are chosen from a group consisting of a) a V-unsaturated alkyl group b) a hydroxyalkyl group having 2 to 6 carbon atoms, both described above; c) an alkyl group having 1 to 22 carbon atoms, cyclic or acyclic and d) an aralkyl group, that is benzyl and substituted benzyl moieties including fused ring moieties having linear or branched chains of 1 to 22 carbon atoms in the alkyl portion of the arakyl.
The unsaturated alkyl group of R3 and R4 may be linear and branched, cyclic and acyclic, substituted and unsubstituted, containing 1 to 22 carbon atoms.
Representative examples of useful alkyl groups useful as R3 and R4 include methyl; ethyl; propyl; 2-propyl; iso-butyl; cyclopentyl; and cyclohexyl.
The alkyl radicals may be derived from a similar source as the long chain alkyl radical of R2 above. 65 4 GB 2 107 693 A 4 Representative examples of an aralkyl group, that is benzyl and substituted benzyl moieties, would include benzyl and those materials derived from, e.g. benzyl halides, benzhydryl halides, trityl halides, 1- halo-1phenylalkanes wherein the alkyl chain has from 1 to 22 carbon atoms such as 1-halo-l-phenylethane; 1-halo-l-phenyl propane; and 1-halo-l- phenyloctadecane; substituted benzyl moieties such as would be derived from ortho-, meta- and para-chlorobenzyl halides, para- methoxybenzyl halides; ortho-, meta- and para-nitrilobenzyl halides, and ortho-, meta- and para-alkylbenzyl halides wherein the alkyl chain contains from 1 to 22 carbon atoms; and fused ring benzyl-type moieties such as would be derived from 2-halomethylnaphthalene, 9- halomethylanthracene and 9-halomethylphenanthrene, wherein the halo group would be defined as chloro-, bromo-, iodo-, or any other such group which serves as a leaving group in the nucleophilic attack of the benzyl type moiety such that the nucleophile replaces the leaving group on the benzyl type moiety.
A quaternary compound is formed of the above described organic cationic compound and an anionic radical which may be Cl, Brl, N02, OH and C2H302 and mixtures thereof. Preferably the anion is selected from the group consisting of chloride and bromide, and mixtures thereof, and is more preferably chloride, although other anions such as acetate, hydroxide, nitrite, etc., maybe present in the organic cationic 15 compund to neutralize the cation.
Organic cationic salts may be prepared by known methods as disclosed in U. S. 2,355,356,2,775,617 and 3,136,819.
The organic anions useful in this invention may be selected from a wide range of materials providing they are capable of reacting with an orgaic cation and form intercalations with a smectite-type clay as an organic 20 cation-organic anion complex. The molecular weight (gram molecular weight) of the organic anion is preferably 3,000 or less, and more preferably 1,000 or less, and contains at least one acidic moiety per molecule as disclosed herein. The organic anion is preferably derived from an organic acid having a pKA less than about 11.0. As indicated, the source acid must contain at least one ionizable hydrogen having the preferred pKA in order to allow the formation of the organic cationorganic intercalation reaction to occur.
Also useable is any compund which will provide the desired organic anion on hydrolysis. Representative compounds include:
1) acid anhydrides including acetic anhydride, maleic anhydride, succinic anhydride and phthalic anhydride; 2) acid halides including acetyl chloride, octanoyl chloride, lauroyl chloride, lauroyl bromide and benzoyl 30 bromide; 3) 1,1,1-trihalides including 1,1,1-trichloroethane and 1,1,1tribromooetane; and 4) orthoesters including ethylorthoformate and ethylorthostearate.
The organic anions may be in the acid or salt form. Salts may be selected from alkali metal salts, alkaline earth salts, ammonia, and organic amines. Representative salts include: hydrogen, lithium, sodium, 35 potassium, magnesium, calcium, barium, ammonium and organic amines such as ethanolamine, diethanolamine, triethanolamine, methyl diethanolamine, butyl diethanolamine, diethyl amine, dimethyl amine, triethyl amine, dibutyl amine, and so forth, and mixtures thereof. The most preferred salt is sodium as the alkali metal salt.
Exemplary types of suitable acidic functional organic compounds useful in this invention include: 40 1) Carboxylic acids including:
a) benzene carboxylic acids such as benzoic acid, ortho-, meta- and paraphthalic acid, 1,2,3 benzenetricarboxylic acid; 1,2,4-benzenetricarboxylic acid, 1,3,5- benzenetricarboxylic acid; 1,2,4,5 benzenetetracarboxylic acid; 1,2,3,4,5,6-benzenehexacarboxylic acid (mellitic acid); b) alkyl carboxylic acids having the formula H-(CH2)n - COOH, wherein n is a number from 0 to 20, such 45 compounds include acetic acid; propionic acid; butanoic acid; pentanoic acid; hexanoic acid; heptanoic acid; octanoic acid; nonanoic acid; decanoic acid; undecanoic acid; lauric acid; tridecanoic acid; tetradecanoic acid; pentaclecanoic acid; hexadecanoic acid; heptadecanoic acid; octadecanoic acid (stearic acid); nonadecanoic acid; eicosonic acid; c) alkyl dicarboxylic acids having the formula HOOC-(CH2)n -COOH, wherein n is 0 to 8 such as oxalic 50 acid; malonic acid; succinic acid; glutaric acid; adipic acid; pimelic acid; suberic acid; azelaic acid; sebacic acid; d) hydroxyalkyl carboxylic acids such as citric acid; tartaric acids; malic acid; mandelic acid; and 12-hydroxystearic acid; e) unsaturated alkyl carboxylic acids such as maleic acid; fumaric acid; and cinnamic acid; f) fused ring aromatic carboxylic acids such as naphthalenic acid; and anthracene carboxylic acid; and g) cycloaliphatic acids such as cyclohexane carboxylic acid; cyclopentane carboxylic acid; f u ran carboxylic acids.
2) Organic sulfur acids including:
a) sulfonic acids including:
(1) benzenesulfonic acids such as benzenesulfonic acid; phenolsulfonic acid; dodecylbenzenesulfonic acid; benzenedisulfonic acid, benzenetrisulfonic acids; Para- toluenesulfonic acid; (2) alkyl sulfonic acids such as methane sulfonic acid; ethane sulfonic acid; butane sulfonic acid; butane disulfonic acid; sulfosuccinate alkyl esters such as dioctyl succinyl sulfonic acid; and alkyl polyethoxy- succinyl sulfonic acid; 1 GB 2 107 693 A 5 b) alkyl sulfates such as the lauryl half ester of sulfuric acid and the octadecyl half ester of sulfuric acid. 3) Organophosphorus acids including: a) phosphonic acids having the the formula:
0 11 IRP(OW2 wherein R is an aryl group or alkyl having 1 to 22 carbon atoms; b) phosphinic acids having the formula:
0 11 R2P0H wherein R is an aryl group or alkyl group having 1 to 22 carbon atoms such as dicyclohexyl phosphinic acid; dibutyl phosphinic acid; and dilauryl phosphinic acid; c) thiophosphinic acids having the formula:
S 11 R2PSH wherein R is an aryl group or alkyl group having 1 to 22 carbon atoms such as di-iso-butyl dithiophosphinic acid; dibutyl dithiophosphinic acid; dioctadecyl dithiophosphinic acid; d) phosphites, that is diesters of phosphorous acid having the formula: HO-P (OR)2 wherein R is an alkyl group having 1 to 22 carbon atoms such as dioctadecyl phosphite; and e) phosphates, that is diesters of phosphoric acid having the formula:
0 11 HO-P-(M2 wherein R is an alkyl group having 1 to 22 carbon atoms, such as dioctaclecyl phosphate. 35 4) Phenols such as phenol; hydroquinone; t- butylcatechol; p-methoxyphenol; and naphthols. 5) thioacids having the formula:
S 11 R-C-Ofi, and 0 11 R-C-SH, and S 11 R-C-SH wherein R is an aryl group or alkyl group having 1 to 22 carbon atoms, such as thiosalicylic acid; thiobenzoic acid; thioacetic acid; thiolauric acid; and thiostearic acid.
6) Amino acids such as the naturally occurring amino acids and derivatives thereof such as 6-aminohexanoic acid; 12-aminododecanoic acid; N-phenyiglycine; and 3-aminocrotonoic acid.
7) Polymeric acids prepared from acidic monomers wherein the acidic function remains in the polymer chain such as low molecular weight acrylic acid polymers and copolymers; and styrene-maleic anhydride copolymers.
8) Miscellaneous acids and acid salts such as ferrocyanide; ferricyanide; sodium tetraphenylborate; phosphotungstic acid; phosphosilicic acid, or any other such anion which will form a tight ion pair with an organic cation, i.e., any such anion which forms a water insoluble precipitate with an organic cation.
The clays used to prepared the organophilic clay gellants of this invention are smectite-type clays which have a cation exchange capacity of at least 75 milliequivalents per 100 grams of clay. Particularly desirable 6 GB 2 107 693 A 6 types of clay are the naturally-occuring Wyoming varieties of swelling bentonites and like clays and hectorite, a swelling magnesium-lithium silicate clay.
The clays, especially the bentonite type clays, are preferably converted to the sodium form if they are not already in this form. This can conveniently be done by preparing an aqueous clay slurry and passing the slurry through a bed of cation exchange resin in the sodium form. Alternatively, the clay can be mixed with water and a soluble sodium compound such as sodium carbonate, sodium hydroxide and the like, followed by shearing the mixture with a pugmill or extruder.
Smectite-type clays occur naturally or may be prepared synthetically by either a pneurnatolytic or hydrothermal synthesis processes. Representative of such clays are montmorillonite, bentonite, beidellite, hectorite, saponite, and stevensite. The cation exchange capacity of the smectite-type clays can be determined by the well-known ammonium acetate method.
The organophilic clays of this invention can be prepared by admixing the clay, organic cation, organic anion and water together, preferably at a temperature within the range from 20'C to 100'C, more preferably 35'C to 77'C for a period of time sufficient for the organic cation and organic anion complex to intercalate with the clay particles, followed by filtering, washing, drying and grinding.
The compositions of the invention as discussed above find wide utility as rheological additives in non-aqueous fluid systems generally.
The non-aqueous fluid compositions in which the self activating organophilic clays are useful include paints, varnishes, enamels, waxes, epoxies, mastics, adhesives, cosmetics, inks, polyester laminating resins and polyester gel coats, and the like. These fluids may be prepared by any conventional method such as 20 described in U.S. Patent 4,208,218 including colloid mills, roller mills, ball mills, and high speed dispersers in which the pigment materials become well dispersed in the organic vehicle by the high shear used in processing.
The organophilic clay gellant is employed in such compositions in amounts sufficient to obtain the desired rheological properties such as high viscosity at low shear rates, control of sagging of fluid films and 25 prevention of settling and hard packing of pigments present in the nonaqueous fluid compositions.
Amounts of the organophilic clay gellant employed in the non-aqueous fluid system should preferably be between about 0.1% and about 15% based on the weight of the treated non- aqueous fluid system and preferably between 0.3% and 5.0% to yield the desired rheological effects.
The following examples are given to illustrate the invention, but are not deemed to be limiting thereof. All 30 percentages given throughout the specification are based upon weight unless otherwise indicated.
A simple convenient test has been devised to illustrate the enhanced dispersion characteristics of the organophilic clays utilized in this invention and exemplified in the following Examples to show the results potentially obtainable in utilizing the compositions of this invention. The test is called the solvent compatibility test. The solvent compatibility test is conducted by taking a sample of the organophilic clay which is sifted into 10 milliliters of various solvents contained in separate 10 milliliter graduated cylinders. The organophilic clay is added at such a rate that the particles are wetted evenly and clumping is not permitted to occur. The samples are allowed to equilibriate after all the organophilic clay has been added (approximately 30 minutes). The volume occupied by the organophilic clay is then recorded in tenths of a milliliter; this number is called the swelling volume.
The mixture is vigorously shaken 50 times, 10 times horizontally, 40 times vertically, and allowed to stand overnight. The volume occupied by the organophilic clay is again recorded in tenths of a milliliter; this value is called the settling volume.
The swelling volume gives an indication of the compatibility of the organic portion of the organophilic clay with the solvents tested; the settling volume gives an indication of the ease of dispersion of the organophilic 45 clay in that solvent under low shear conditions.
Because of variances in the rate of sifting of the organoclay into the solvent and the vigor with which the sample is shaken, the numbers are not absolute. Small differences in the volumes are not considered significant, rather, the values are intended to be for comparison only.
The inventive organophilic clay gellants employed in the examples were prepared by the following 50 procedure, unless otherwise noted. A 3% clay slurry (sodium form of Wyoming bentonite) and the slurry was heated to 60'C with stirring. The organic anion was added to the clay slurry and reacted for approximately 10 minutes followed by addition of the organic cation. The amounts or organic materials added are setforth in the Tables and expressed in mill i-equivalents of the organic cation and organic anion per 1 OOg of clay, 100% active clay basis. The mixture was then reacted under agitation for a period of time sufficient to complete the 55 reaction (generally 10 to 60 minutes). The organoclay is collected on a vacuum filter. The filter cake is washed with hot (40-BO'C) water and dried at 60'C. The dried organoclay is ground using a hammer mill or similar grinding apparatus to reduce the particle size and then sieved through a 200-mesh screen.
Example 1
Allyl methyl di (hydrogenated-ta 1 low) ammonium xhioride (abbreviated AM2HT).
Placed 824.7 gm. methyl di (hydrogenated-tallow) amine, approximately 350mi. isopropyl alcohol, 250 gm. NaHC03,191.3 gm. allyl chloride, and 10 gm. ally] bromide (as a catalyst) in a 4-liter reaction vessel equipped with a condenser and mechanical stirrer. The misture was heated and allowed to reflux gently.
Periodically, samples were removed, filtered, and titrated with standardized HCl and NaOH. The reaction was 65 7 GB 2 107 693 A 7 considered complete when there was 0.0% amine HCI and 1.8% amine. The final analysis showed an effective gram molecular weight of 831.17.
Examples 2-4
A 3% clay slurry, the sodium form of Wyoming bentonite in Examples 2 and 3 and hectorite in Example 4, 5 was heated to 60C with stirring. A solution of organic cationic compound, ethanol methyl d i (hydrogenated tallow) ammonium chloride [EM2HTI, for Example 2, and AM2HT prepared in Example 1 for examples 3 and 4, was added to the clay slurry and stirred for 20 minutes. The organoclay was collected on a vacuum filter.
The filter cake was washed with 60'C water and dried at 600C. The dried organoclay was ground using a hammer mill to reduce the particle size and then sieved through a U.S. Standard 200 mesh screen.
Examples 5-24
These examples demonstrate the preparation of organophilic clays of this invention using various organic anions and ally] methyl di(hydrogenatedtallow) ammonium chloride (AM2HT) as the organic cation. A conventional organophilic clay using AM2HT as the organic cation is presented as a comparative example.15 The compositions are set forth in Table 1 with the solvent compatibility results in Table 1(a). The data illustrates the superior dispersion characteristics of the inventive organophilic clays as compared with organophilic clays prepared in the absence of the organic anion.
8 GB 2 107 693 A TABLE 1
8 Organic Organic Anion Catfin Example M. E. M. E. 5 No. OrganicAnion (Salt) Ratio Ratio Na Benzoate 15 115 6 Na Benzoate 22.5 122.5 10 7 Na Benzoate 30 130 8 Na Benzoate 10 110 15 9 Na Benzoate 22.5 130 Na p-Phenoisuifonate 15 115 11 Na p-Phenoisuifonate 30 130 20 12 Na p-Phenoisuifonate 22.5 122.5 13 Na p-Phenoisuifonate 10 110 25 14 Na Salicylate 30 130 Na Salicylate 22.5 122.5 16 Na Salicylate 15 115 30 17 Na Dioctadecyl Phosphite 22.5 122.5 18 Benzoic Acid 22.5 122.5 35 19 Disodium Phthalate 22.5 122.5 Na Octoate 22.5 122.5 21 Na Stearate 22.5 122.5 40 22 Na Laurate 22.5 122.5 23 Na 1 2-Hyd roxystea rate 22.5 122.5 45 24 Na3 Citrate 22.5 122.5 Comparative None None 114 9 TABLE 1 (a)
Solvent Compatibility Solvent 60140 Di-Isodecyl GB 2 107 693 A 9 Toluene Methyl isobutyl ketone Phthalatel Toluene Heptane Example Swelling Settling Swelling Settling Swelling Settling Swelling Settling No. Volume Volume Volume Volume Volume Volume Volume Volume 10 10 100 12 19 10 8 18 27 6 10 100 11 18 8 10 28 33 7 15 100 11 17 8 8 28 42 15 8 8 76 10 20 7 8 10 12 9 8 80 14 20 10 10 30 44 20 12 78 13 16 11 14 14 18 11 12 48 12 18 8 10 22 68 12 8 100 12 14 10 12 27 32 25 13 12 68 13 17 10 11 9 12 14 16 100 14 19 10 14 26 34 30 11 100 12 18 9 10 23 29 16 12 100 12 17 9 9 16 22 17 7 100 12 16 10 5 20 26 35 18 8 32 13 17 7 8 22 70 19 10 100 14 18 9 8 20 52 40 12 36 14 20 7 8 32 57 21 11 100 13 19 8 11 58 44 22 12 100 13 17 8 9 32 37 45 23 14 100 12 18 10 10 37 44 24 10 100 12 20 10 11 34 52 50 Comparative 15 88 13 16 16 20 7 11 GB 2 107 693 A Examples 24-25 These examples demonstrate the preparations of organophilic clays of this invention using various organic anions and diallyl di(hydrogenated tallow) ammonium chloride as (2A2HT) organic cation. A conventional organophilic clay using 2A2HT as the organic cation is presented as a comparative example.
The compositions are set forth in Table 11 with the solvent compatability results in Table ll(a). The data 5 illustrates the much superior dispersion characteristics of the inventive organopinflic clays as compared with organophilic clays prepared in the absence of the organic anion.
TABLE 11
Organic Organic Anion Cation Example M. E. M. E.
No. Organic Anion (Salt) Ratio Ratio 15 Na Salicylate 22.5 129.4 26 Na Napthalene 1-Carboxylate 22.5 129.4 27 Na p-Toluate 22.5 122.5 20 28 Na Borate 22.5 122.5 29 Disodium Phthalate 22.5 122.5 25 Na Benzoate 22.5 129.4 31 Na Ferricyanide 22.5 122.5 32 Na Tetra phenyl bo rate 22.5 122.5 30 33 Na 1-Butanesulfonate 22.5 122.5 34 Na p-Toluenesulfonate 22.5 122.5 35 Na Benzenesuffonate 22.5 122.5 36 Na Benzene-11,3-sulfonate 22.5 122.5 37 p-PhenoIsulfonate 22.5 122.5 40 38 Na 1 2-Hyd roxystea rate 22.5 122.5 39 Na Oleate 22.5 122.5 45 Na Stearate 22.5 122.5 41 Na Laurate 22.5 122.5 42 Na Octoate 22.5 122.5 50 43 Na 2-Ethylhexanoate 22.5 122.5 44 Na Hexanoate 22.5 122.5 55 Na Dodecylbenzenesulfonate 22.5 122.5 Comparative None None 110 11 GB 2 107 693 A 11 TABLE 11(a)
Solvent Compatibility Solvent 60140 Di-isodecyl Toluene Methyl isobutyl ketone Phthalatel Toluene Lacquer Solvent Example Swelling Settling Swelling Settling Swelling Settling Swelling Settling No. Volume Volume Volume Volume Volume Volume Volume Volume 10 34 18 12 26 26 14 37 12 16 13 13 14 - 80 27 13 28 12 16 10 12 14 23 15 28 10 57 11 17 11 10 16 100 29 15 37 12 18 12 11 16 22 20 54 18 13 87 31 9 53 11 16 10 13 18 33 32 10 5 11 14 9 10 -- -- 25 33 12 73 10 12 10 12 15 88 34 13 18 11 14 11 12 14 82 30 12 16 12 14 10 12 16 88 36 14 38 12 15 12 13 14 22 37 14 45 12 11 12 12 14 80 35 38 14 46 12 14 10 14 16 84 39 16 30 12 18 12 12 14 78 40 14 100 18 32 16 90 18 94 41 14 32 12 18 10 10 16 80 42 14 52 12 20 12 14 16 100 45 43 14 64 10 16 10 12 15 80 44 10 54 12 20 10 14 17 82 50 12 12 12 13 9 10 12 50 Comparative 14 33 12 14 12 15 16 22 12 GB 2 107 693 A Examples 46-58 These examples demonstrate the preparations of organophilic clays of this invention using various organic anions and ethanol climethyl hydrogenated tallow ammonium chloride (E2MHT) as the organic cation. A conventional organophilic clay using E2MHT as the organic cation is presented as a comparative example. The compositions are set forth in Table III with the solvent compatibility results in Table 111(a). The data illustrates the much superior disperson characteristics of the inventive organophilic clays as compared 12 with organophilic clays prepared in the absence of the organic anion.
TABLE Ill
Organk Organic Anion Cation Example M.E. M.E.
No. Organic Anion (Salt) Ratio Ratio 15 46 Na Benzoate 22.5 114 47 Na Benzoate 30 130 48 Na Benzoate 22.5 122.5 20 49 Na Phenolate 22.5 122.5 Na Tetraphenylborate 22.5 122.5 25 51 Na Ferrocyanide 22.5 122.5 52 Na Fluorescein Derivative 22.5 122.5 53 Rose Benzal 22.5 122.5 30 54 Disodium Phthalate 22.5 122.5 Na Laurate 22.5 122.5 35 56 Na Octoate 22.5 122.5 57 Na Stearate 22.5 122.5 58 Na Abietate 22.5 122.5 40 Comparative None None 108.1 c r 13 GB 2 107 693 A 13 60140 Di-isodecyl Toluene Methyl isobutyl ketone Phthalatel Toluene Heptane Example Swelling Settling Swelling Settling Swelling Settling Swelling Settling No. Volume Volume Volume Volume Volume Volume Volume Volume 5 46 13 18 18 24 10 12 16 18 47 20 46 19 29 14 16 20 32 48 14 22 20 26 14 14 16 24 10 49 18 28 18 26 14 15 20 28 12 22 18 30 13 15 20 28 15 51 14 26 22 38 9 10 17 26 52 16 30 19 28 10 13 21 30 53 16 26 21 27 11 12 22 28 20 54 18 36 22 30 18 21 -- - 16 33 18 26 14 18 -- - 25 56 17 30 22 28 14 18 57 17 24 12 16 10 12 58 17 30 23 32 12 12 -- -- 30 Comparative 6 8 17 19 8 10 12 14 71 14 GB 2 107 693 A Examples 59-72 These examples demonstrate the preparations of organophilic clays of this invention using various organic anions as and various quaternary ammonium chlorides as the organic A conventional organophilic clay using ethanol methyl di(hydrogenated tallow) as the organic cation is presented as a comparative example. The compositions are set forth in Table IV with the solvent compatibility results in Table IV(a). The data illustrates the much superior dispersion characteristics of the inventive organophilic clays as compared with organophilic clays prepared in the absence of the organic anion.
TABLE IV.
Organic Organic Cation Anion M. E. M. E. Ratio Ratio 122.5 22.5 122.5 22.5 122.5 22.5 20 122.5 22.5 122.5 22.5 30 122.5 22.5 122.5 22.5 30 122.5 22.5 122.5 22.5 122.5 22.5 122.5 22.5 122.5 22.5 40 15 108.2 Example No.
59 61 62 63 64 66 67 68 69 72 Comparative 14 Organic Cation Allyl Dimethyl Hydrogenated Tallow Ally] Dimethyl Hydrogenated Tallow Allyl Dimethyl Hydrogenated Tallow Allyl Dimethyl Hydrogenated Tallow Ally[ Dimethyl Hydrogenated Tallow Ethanol Methyl Difflydrogenated Tallow) Ethanol Methyl Di(I-1ydrogenated Tallow) Ethanol Methyl Di(I-1ydrogenated Tallow) Ethanol Methyl Difflydrogenated Tallow) Diallyl Methyl Octadecyl Trially] Hydrogenated Tallow Triethanol Hydrogenated Tallow Treithanol Hydrogenated Tallow Triethanol Hydrogenated Tallow Ethanol Methyl Difflydrogenated Tallow) OrganicAnion Na2 Phthalate Na Octoate Na Laurate Na Stearate Na Abietate Na Benzoate Na 9,10-Epoxystearate Na Dioctadecyl Phosphite Na Oleate Na2 Phthalate Na2 Phthalate Na2 Phthalate Na Benzoate Na Benzoate None Example No.
59 61 62 63 64 66 67 68 69 71 TABLE IV(a)
Solvent Compatibility Solvent Toluene Swelling Settling Volume Volume 16 18 18 12 14 13 16 12 12 11 Comparative 12 46 80 78 78 78 72 50 84 20 51 31 22 25 15 18 Methyl isobutyl ketone Swelling Settling Volume Volume 14 16 18 24 14 12 14 16 28 14 12 13 16 12 21 32 42 38 40 12 18 81 26 94 20 22 26 20 14 60140Di-isodecyl Phthalatel Toluene Swelling Settling Volume Volume 14 18 16 17 16 9 14 18 12 22 14 11 12 11 11 13 10 10 10 10 8 14 18 16 42 15 13 14 12 14 GB 2 107 693 A 15 Heptane Swelling Settling Volume Volume 13 20 24 100 24 100 24 100 24 100 12 -- -- 25 12 14 14 13 14 51 17 20 26 16 16 16 GB 2 107 693 A 16 Examples 73-79 These examples demonstrate the preparations of organophilic clays of this invention using various organic anions and diethanol methyl hydrogenated tallow ammonium chloride (2EMI-IT) as the organic cation. A conventional organophilic clay using 2EMHT as the organic cation is presented as a comparative example. The compositions are set forth in Table V with the solvent compatibility results in Table V(a). The 5 data illustrates the much superior dispersion characteristics of the invention organophilic clays as compared with organophilic clays prepared in the absence of the organic anion.
TABLE V
Organic Organic Anion Cation Example M. E. M. E.
No. Organic Anion (Salt) Ratio Ratio 15 73 Na Benzoate 15 115 74 Na Benzoate 15 122.5 75 Na2 Phthalate 22.5 122.5 20 76 Na Octoate 22.5 122.5 77 Na Laurate 22.5 122.5 9- 5 78 Na Stearate 22.5 122.5 79 Na Abietate 22.5 122.5 Comparative None None 111.7 30 z W TABLE V (a)
Solvent Compatibility Solvent 60140 Di-isodecyl Toluene Methyl isobutyl ketone PhthalatelToluene n-ButylAcetate Swelling Settling Swelling Settling Swelling Settling Swelling Settling No. Volume Volume Volume Volume Volume Volume Volume Volume 40 73 8 10 22 26 8 9 16 20 74 9 14 15 35 10 12 16 24 45 10 12 18 20 10 10 16 17 76 10 14 18 26 8 10 -- -- 77 9 12 18 26 8 9 50 78 3 3 12 12 4 4 79 5 5 27 32 2 2 55 Comparative 4 4 19 22 5 8 14 17 The invention being thus described, it will be obvious that the same may be varied in many ways. Such variations are not to be regarded as a departure from the spirit and scope of the invention and all such modifications are intended to be included within the scope of the following claims.
f V 17
Claims (19)
1. An organophilic clay gellant, which comprises the reaction product of: a. an organic cation salt compound, wherein said organic cation has the formula:
R, 1 Rh.- X- RZ 1 R5 GB 2 107 693 A 17 wherein R, is selected from the group consisting of a 0, V-unsaturated alkyl group, and a hydroxyalkyl group having 2 to 6 carbon atoms, and mixtures thereof; R2 is a long chain alkyl group having 12 to 60 carbon atoms; R:3 and R4 are individually selected from the group consisting of a P, y-unsaturated alkyl group, a hydroxyalkyl group having 2to 6 carbon atoms, an aralkyl group, an alkyl group having from 1 to 22 carbon 20 atoms and mixtures thereof; X is selected from a group consisting of phosphorous and nitrogen; b. an organic anion; and c. a smectite-type clay having a cation exchange capacity of at least 75 milliequivalents per 100 grams of said clay; such that an organic cation-organic anion complex is intercalated with the smectite-type clay and the cation exchange sites of the smectite-type clay are substituted with the organic cation.
2. The gellant of Claim 1, wherein the P,y-unsaturated alkyl group is selected from a group consisting of cyclic groups, acyclic alkyl groups having less than 7 carbon atoms, acyclic alkyl groups substituted with aromatic groups, and aromatic groups substituted with aliphatic groups.
3. The gellant of Claim 1 wherein the hydroxyalkyl group is selected from a group consisting of cyclic groups and aliphatic groups having 2 to 6 carbon atoms with the hydroxy substitution on C2tO C6.
4. The gellant of Claim 1 wherein R2 has from 12 to 22 carbon atoms.
5. The gellant of Claim 4 wherein R2 is along chain fatty acid group.
6. The gellant of Claim 1 wherein the organic anion is derived from an organic acid having a pKA less than about 11.0.
7. The gellant of Claim 1 wherein the smectite-type clay is selected from the group consisting of hectorite 35 and sodium bentonite.
8. The gellant of Claim 1 wherein the amount of said organic anion is from 5 to 100 milliequivalents per 100 grams of said clay, 100% active clay basis.
9. The gellant of Claim 1 wherein the amount of said organic cation is sufficient to satisfy the cation exchange capacity of the smectite-type clay and the cationic exchange capacity of the organic anion.
10. The geilant of Claim 1 wherein the amount of said organic cation is from 80to 200 milliequivalents per 100 grams of clay, 100% active clay basis.
11. The gellant of Claim 1 wherein the amount of said organic cation is from 100 to 160 milliequivalents per 100 grams of clay, 100% active clay basis.
12. A process for preparing an organophilic clay gellant which comprises:
a. preparing an aqueous slurry of smectite-type clay, said clay ranging from about 1 to about 80% by weight of slurry; b. heating the slurry to a temperature between 2WC and 100OC; c. adding from about 5to 100 milliequivalents of an organic anion per 100 grams of clay, 100% active clay basis and an organic cation compound, wherein said organic cation has the formula:
1 3 R, 1 1 Rit.- X- RZ 1 i 1 1 + 1 i RS 1 J 60 wherein R, is selected from the group consisting of a P, y-unsaturated alkyl group and a hydroxyalkyl group having 2 to 6 carbon atoms, and mixtures thereof; R2 is a long chain alkyl group having 12 to 60 carbon atoms; R3 and R4 are individually selected from the group consisting of a P, V-unsaturated alkyl group, a hydroxyalkyl group having 2 to 6 carbon atoms, an aralkyl group, an alkyl group having from 1 to 22 carbon 65 18 GB 2 107 693 A 18 atoms and mixtures thereof; X is selected from a group consisting of phosphorous and nitrogen; said organic cation compound is used in a sufficient amount to satisfy the cation exchange capacity of the smectite- type clay and the cationic activity of the organic anion while agitating the reaction solution; d. reacting the mixture fora sufficient time to form a reaction product comprising an organic cation-organic anion complex which is intercalated with the smectite-type clay and the cation exchange sites 5 of the smectite-type clay are substituted with the organic cation; and e. recovering the reaction product.
13. The process of Claim 12 wherein the organic cation is selected from the group consisting of quaternary ammonium salts, phosphonium salts and sulfonium salts containing at least one lineal or branched alkyl group having 8 to 22 carbon atoms.
14. The composition of Claim 12 wherein the organic anion is derived from an organic acid having a pKA less than about 11.0.
15. The composition of Claim 12 wherein the smectitie-type clay is selected from the group consisting of hectorite and sodium bentonite.
16. The composition of Claim 12 wherein the amount of said organic anion is from 10 to 50 milliequivalents per 100 grams of said clay, 100% active clay basis.
17. The composition of Claim 12 wherein the amount of said organic cation compound is from 80 to 200 milliequivalents per 100 grams of clay, 100% active clay basis.
18. The process of Claim 12 wherein the organic action is added to the smectite-type clay prior to the addition of the organic cation compound.
19. The process of Claim 12 wherein the organic anion and organic cation compund are added to the smectite-type clay in the form of an organic cation-organic anion complex.
Printed for Her Majesty's Stationery Office, by Croydon Printing Company Limited, Croydon, Surrey, 1983. Published by The Patent Office, 25 Southampton Buildings, London, WC2A lAY, from which copies may be obtained.
il 4 1
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US06/313,033 US4434075A (en) | 1981-10-19 | 1981-10-19 | Anionically modified organophilic clays and their preparation |
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GB2107693A true GB2107693A (en) | 1983-05-05 |
GB2107693B GB2107693B (en) | 1985-06-26 |
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GB08134467A Expired GB2107693B (en) | 1981-10-19 | 1981-11-16 | Organophilic organic-clay complexes |
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US (1) | US4434075A (en) |
JP (1) | JPS5867338A (en) |
AU (1) | AU545724B2 (en) |
BE (1) | BE891144A (en) |
BR (1) | BR8107423A (en) |
CA (1) | CA1173055A (en) |
CH (1) | CH650228A5 (en) |
DK (1) | DK506881A (en) |
FR (1) | FR2514775B1 (en) |
GB (1) | GB2107693B (en) |
GR (1) | GR76348B (en) |
IE (1) | IE52430B1 (en) |
IT (1) | IT1194107B (en) |
MX (1) | MX160752A (en) |
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1981
- 1981-10-19 US US06/313,033 patent/US4434075A/en not_active Expired - Fee Related
- 1981-11-16 CH CH7368/81A patent/CH650228A5/en not_active IP Right Cessation
- 1981-11-16 IT IT25108/81A patent/IT1194107B/en active
- 1981-11-16 FR FR8121401A patent/FR2514775B1/en not_active Expired
- 1981-11-16 AU AU77517/81A patent/AU545724B2/en not_active Ceased
- 1981-11-16 NO NO813867A patent/NO813867L/en unknown
- 1981-11-16 JP JP56182410A patent/JPS5867338A/en active Granted
- 1981-11-16 DK DK506881A patent/DK506881A/en not_active Application Discontinuation
- 1981-11-16 IE IE2674/81A patent/IE52430B1/en unknown
- 1981-11-16 SE SE8106794A patent/SE8106794L/en not_active Application Discontinuation
- 1981-11-16 CA CA000390168A patent/CA1173055A/en not_active Expired
- 1981-11-16 BR BR8107423A patent/BR8107423A/en unknown
- 1981-11-16 BE BE0/206563A patent/BE891144A/en not_active IP Right Cessation
- 1981-11-16 GB GB08134467A patent/GB2107693B/en not_active Expired
- 1981-11-16 GR GR66528A patent/GR76348B/el unknown
- 1981-11-17 MX MX190158A patent/MX160752A/en unknown
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4752342A (en) * | 1983-11-05 | 1988-06-21 | Perchem Limited | Organoclay materials |
US4558075A (en) * | 1984-03-30 | 1985-12-10 | Ppg Industries, Inc. | High-solids coating composition for improved rheology control containing organo-modified clay |
US4620993A (en) * | 1984-03-30 | 1986-11-04 | Ppg Industries, Inc. | Color plus clear coating system utilizing organo-modified clay in combination with organic polymer microparticles |
US4620994A (en) * | 1984-03-30 | 1986-11-04 | Ppg Industries, Inc. | Color plus clear coating system utilizing organo-modified clay |
GB2158053A (en) * | 1984-04-27 | 1985-11-06 | English Clays Lovering Pochin | Organo-clays |
GB2185246A (en) * | 1985-10-28 | 1987-07-15 | Nl Chemicals Inc | Preactivated organophilic clay gellant |
GB2185246B (en) * | 1985-10-28 | 1989-10-18 | Nl Chemicals Inc | Preactivated organophilic clay gellant |
Also Published As
Publication number | Publication date |
---|---|
NO813867L (en) | 1983-04-20 |
IE52430B1 (en) | 1987-10-28 |
FR2514775A1 (en) | 1983-04-22 |
GR76348B (en) | 1984-08-06 |
IE812674L (en) | 1983-04-19 |
SE8106794L (en) | 1983-04-20 |
IT8125108A0 (en) | 1981-11-16 |
CH650228A5 (en) | 1985-07-15 |
FR2514775B1 (en) | 1986-07-04 |
BR8107423A (en) | 1983-05-24 |
GB2107693B (en) | 1985-06-26 |
CA1173055A (en) | 1984-08-21 |
AU7751781A (en) | 1983-04-28 |
US4434075A (en) | 1984-02-28 |
MX160752A (en) | 1990-05-09 |
JPH0249774B2 (en) | 1990-10-31 |
IT1194107B (en) | 1988-09-14 |
DK506881A (en) | 1983-04-20 |
JPS5867338A (en) | 1983-04-21 |
BE891144A (en) | 1982-03-16 |
AU545724B2 (en) | 1985-07-25 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19941116 |